Chemistry:7-Acetoxymitragynine
From HandWiki
7-Acetoxymitragynine is an opioid drug which is a semi-synthetic derivative of 7-hydroxymitragynine, a natural product derived from the South-East Asian tree kratom. It can be derived by acetylation of the hydroxyl group of 7-hydroxymitragynine, for instance with acetic anhydride, but can also be produced directly from mitragynine by reaction with Lead(IV) acetate, and is a common synthetic intermediate in the production of 7-hydroxymitragynine from crude kratom extracts. Unlike the higher potency seen with acetyl esters of some other opioids such as morphine, 7-acetoxymitragynine is less potent than 7-hydroxymitragynine, but nevertheless retains opioid activity and has been sold as a designer drug since around 2006.[1][2][3][4][5]
See also
- MGM-15
- 6-Monoacetylmorphine
References
- ↑ "Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands". Journal of Medicinal Chemistry 45 (9): 1949–1956. April 2002. doi:10.1021/jm010576e. PMID 11960505.
- ↑ "Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa". Chemical & Pharmaceutical Bulletin 52 (8): 916–928. August 2004. doi:10.1248/cpb.52.916. PMID 15304982.
- ↑ "Orally active opioid compounds from a non-poppy source". Journal of Medicinal Chemistry 56 (12): 4840–4848. June 2013. doi:10.1021/jm400143z. PMID 23517479.
- ↑ Kratom and Other Mitragynines. 2014. doi:10.1201/b17666. ISBN 978-1-4822-2519-8.
- ↑ "Asymmetric Total Syntheses of Mitragynine, Speciogynine, and 7-Hydroxymitragynine". Chemical & Pharmaceutical Bulletin 70 (9): 662–668. 2022. doi:10.1248/cpb.c22-00441. PMID 36047237.
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